Executive Assistant to the Chief Technology Officer

Randstad Staffing is currently looking for experienced Executive Assistants to join one of our top insurance clients in Toronto to support their Chief Technology Officer (CTO).
We are seeking a highly organized, detail-oriented, and forward-thinking Executive Assistant.
In this role, you will serve as a strategic partner, trusted advisor, and operational anchor, enabling the CTO to focus on driving innovation, technical strategy, and global leadership.

The ideal candidate is a self-starter who thrives in a fast-paced, high-growth environment. You are not only comfortable with technology, you embrace it. You bring a creative, solutions-oriented mindset, exceptional communication skills, and a deep understanding of how to support and anticipate the needs of senior executives and their stakeholders.

Salary - ranges between $58,000 - $100,000

Full time permanent role in Toronto

Hybrid - 4 days on site

Advantages
Full time, Permanent role
Company share ownership program
Pension and savings programs, with company-matched RRSP contributions
Paid volunteer days and company matching on charitable donations
Educational resources, tuition assistance, and paid time off to study for exams
Focus on inclusion with employee groups, support for gender affirmation surgery, access to BIPOC counsellors, access to programs for working parents
Wellness and recognition programs
Discounts on products and services

Responsibilities
- Own and optimize the CTO’s complex calendar. With an understanding of key goals and deliverables, prioritize meetings, resolve conflicts, and proactively anticipate scheduling needs across a diverse stakeholder group including C-suite and external partners.
- Plan and manage intricate domestic and international travel itineraries, including flights, accommodations, ground transportation, and visas. Prepare accurate and timely expense reports with a high degree of precision.
- Serve as a key liaison and gatekeeper actively triaging incoming communications. Draft, review, and manage high-level communications, ensuring clarity, professionalism, and alignment with the CTO’s voice and priorities.
- Lead the planning and execution of internal and external meetings, off-sites, technical summits, and strategic events. Coordinate logistics, prepare briefing materials, and ensure seamless follow-up.
- Maintain highly organized digital and physical filing systems, ensuring critical documents, research, and data are easily accessible and secure. Track key deliverables, deadlines, and documents to ensure the CTO is always prepared and informed.
- Handle a wide range of highly sensitive and confidential information with unwavering discretion, integrity, and professionalism, including intellectual property, strategic plans, personnel matters, and pre-release technologies.
- Build and maintain strong working relationships across the organization and external partners, representing the CTO’s office with warmth, professionalism, and a deep understanding of stakeholder needs.
- Bring a creative lens to challenges. Whether it’s streamlining a process or improving a communication flow, you’re always looking for ways to enhance efficiency and impact.
- Think several steps ahead. Proactively identify opportunities, flag potential issues and propose solutions such as pre-booking necessary resourcing and monitoring upcoming deadlines.
- Other general administrative duties as needed

Qualifications
- 5+ years of demonstrable experience as an Executive Assistant supporting C-level executives, preferably within a fast-paced technology, organization.
- A college diploma or equivalent practical experience.
- Exceptional organizational skills, meticulous attention to detail, and the ability to manage multiple priorities simultaneously without compromising quality.
- Strong written and verbal communication skills.
- Proficient with modern office suites (e.g., Microsoft Office 365 – particularly Calendar, Docs/Word, Sheets/Excel, Slides/PowerPoint
- Proven track record of handling highly confidential information with the utmost integrity and professionalism.
- A self-starter who takes initiative, anticipates needs, identifies problems, and proposes solutions with minimal oversight.
- Ability to thrive in a dynamic, rapidly evolving environment, adapting to changing priorities and tight deadlines with a positive attitude.
- Strong ability to build rapport, influence without authority, and collaborate effectively with diverse personalities and work styles.


Summary
If this role interests you, please apply on randstad.ca or you can email me at virangana.shah@randstad.ca

We appreciate all applications, however, only those who meet the requirements for this role will be contacted.

Randstad Canada is committed to building a diverse workforce reflective of the diversity of Canada. As a result, we promote employment equity and encourage candidates, especially those who identify as a woman, an Aboriginal person, a person with a disability or a member of a visible minority group, and any others who may contribute to the diversification of our workforce, to apply.
Randstad Canada is also committed to developing an inclusive, barrier-free selection processes and work environments. If contacted in relation to a job opportunity, you should advise your Randstad Representative or your local Randstad branch in a timely fashion of the accommodation measures which must be taken to enable you to be assessed in a fair and equitable manner. Information received relating to accommodation measures will be addressed confidentially.

Randstad Canada is committed to fostering a workforce reflective of all peoples of Canada. As a result, we are committed to developing and implementing strategies to increase the equity, diversity and inclusion within the workplace by examining our internal policies, practices, and systems throughout the entire lifecycle of our workforce, including its recruitment, retention and advancement for all employees. In addition to our deep commitment to respecting human rights, we are dedicated to positive actions to affect change to ensure everyone has full participation in the workforce free from any barriers, systemic or otherwise, especially equity-seeking groups who are usually underrepresented in Canada's workforce, including those who identify as women or non-binary/gender non-conforming; Indigenous or Aboriginal Peoples; persons with disabilities (visible or invisible) and; members of visible minorities, racialized groups and the LGBTQ2+ community.

Randstad Canada is committed to creating and maintaining an inclusive and accessible workplace for all its candidates and employees by supporting their accessibility and accommodation needs throughout the employment lifecycle. We ask that all job applications please identify any accommodation requirements by sending an email to accessibility@randstad.ca to ensure their ability to fully participate in the interview process.